There was a time when Boston Harbor sprouted a bizarre forest of trees taller than any found on land in New England. Rather than leaves or the evergreen needles synonymous with the region, these floating trees seemed to grow massive squares of pale fabric, with tufts of color fluttering over their tops.

Before steam, coal, oil and gasoline, it was wind that powered the commerce of Boston, filling the harbor with the masts and sails of towering tall ships. Once as commonplace in Boston Harbor as today’s traffic is on Commonwealth Ave., they have now all but vanished. There are, however, several locations hidden along the waterfront where the tall ship experience has been preserved.

Meet the Crew

Nestled between the aquarium and the Boston Marriott Long Wharf are two schooners modeled after classic tall ship designs—the 125-foot Liberty Clipper and the 67-foot Liberty Star—both belonging to the Liberty Fleet of Tall Ships. These ships give visitors the opportunity to experience what it was like to sail on the boats that once crowded Boston Harbor.

Don’t expect costumed actors armed with cutlasses and history lessons though; instead you’ll meet Ben, the sailor/bartender/hostel proprietor/cook-if-the-real-cook-is-missing, who has been living on the Liberty Clipper for the past two years. There’s also Doug, the first mate who quit his decades-long career as a software engineer to turn his pastime of sailing into a lifestyle; Christopher, a former chef of 22 years with the charm of an Alabaman and the cool of a surf bum; and Noah, the bearded captain who has been sailing on the Liberty Clipper for close to ten years.

Bar to Bunk

This is just half of the suntanned and lighthearted crew that takes visitors out on the Liberty schooners to cruise Boston Harbor up to eight times per day. While on the water, visitors are invited to help raise the sails and be as involved in the sailing of the boat as they wish. There is a full bar onboard and, dependent on the wind, sights will include Fort Independence, fellow tall ship the USS Constitution and unparalleled views of Boston from the water.

Both boats are available for private event charters, from corporate outings to wedding ceremonies and receptions; the Liberty Clipper can accommodate 110 guests and the Star, 39. When the boats dock for the night the Liberty schooners convert into one of the most unique—and best priced—lodging experiences in the city. In the vein of a hostel, for $60 travelers can spend the night onboard in a shared cabin, or for $120 they can book a private cabin with two bunks.

Two Six Heave!

The Liberty tall ships are about as authentic an historic sailing experience as you can find today. What could better emulate the bygone day of the tall ship than sailing with actual contemporary sailors who have exchanged regular office jobs for a life hauling line on classically rigged schooners? It is a wonder to hear Captain Noah call an order from the stern, listen as it is relayed forward in repeated calls then watch the barefooted crewmen seamlessly bound across the deck, unhitching line from belaying pins and hauling in unison: “Two six HEAVE!”

Tomorrow's History

Doug, the first mate, says that one of the best parts of his job is forever becoming a part of people’s experience with the city: “In the time these boats have been sailing, you couldn’t hope to count the number of visitors who have come and gone on these decks.” The tall ships, he said, not only preserve what is already history in Boston, but also create new experiences and memories for those who pass through.

“There’s nothing quite like having somebody six-feet tall walk up and say ‘Hey I remember you,’ and the last time you saw them they were four-foot flat and holding their mother's hand as they ambled on deck.”